As usual, find the solution to your own problem the minute you ask for help. Saw someone else having a similar problem, and they realized that the way they were mounting didn't mean anything to Wine, so with some modifications I've now got it set up such that Wine knows what it's doing. This problem, at least, is solved. For anyone else having the same issue: Do not do a doubleclick mount, use: sudo mount -o loop filepath pathwineknowstoseekcd E.g. I use /media/cdrom0 as my disc drive in wine, so I did sudo mount -o loop loldisc.iso /media/cdrom0 If you're wondering why I stated disc when my issue became related to it being a poorly mounted .iso, it's because I ripped the iso myself (my cd drive has a distressing habit of vibrating insanely) and thought I'd mounted it correctly.
